40+ Houses for Sale in Winchester, MA
44 results
44 single-family homes are for sale in Winchester, MA (median list price $1,749,000), as of November 7, 2026.
$1,499,000
Price reduced by ↓ $100,0004 Churchill Road, Winchester, MA 01890
$619/sqft · 62 days on market
$1,650,000
117 Highland, Winchester, MA 01890
$443/sqft · 60 days on market
$1,599,000
9 Watson Pl, Winchester, MA 01890
$833/sqft · 2 days on market
$1,749,000
17 Churchill Rd, Winchester, MA 01890
$499/sqft · 61 days on market
$3,295,000
Price reduced by ↓ $155,0007 Hutchinson Road, Winchester, MA 01890
$575/sqft · 90 days on market
What's actually happening in Winchester right now?
Forget the national headlines. Get the hyper-local, street-level data on inventory, price drops, and true market value before you make an offer.
$999,000
Price reduced by ↓ $26,00053 Lake Street, Winchester, MA 01890
$447/sqft · 178 days on market
$899,000
Price reduced by ↓ $51,00047 Water Street, Winchester, MA 01890
$663/sqft · 116 days on market
$1,449,000
15 Madison Ave W, Winchester, MA 01890
$508/sqft · 2 days on market
$815,000
Price reduced by ↓ $75,00080 Nelson St, Winchester, MA 01890
$547/sqft · 24 days on market
$1,699,000
3 Sunset Road, Winchester, MA 01890
$621/sqft · 10 days on market
$919,000
Price reduced by ↓ $55,900258 Cross St, Winchester, MA 01890
$535/sqft · 59 days on market
$2,995,000
Price reduced by ↓ $205,0009 Albamont Road, Winchester, MA 01890
$491/sqft · 249 days on market
$1,744,000
Price reduced by ↓ $5,0001 Town Way, Winchester, MA 01890
$579/sqft · 103 days on market
$2,149,000
Price reduced by ↓ $50,00019 Hancock Street, Winchester, MA 01890
$602/sqft · 61 days on market
$2,750,000
Price reduced by ↓ $49,00014 Nassau Drive, Winchester, MA 01890
$395/sqft · 208 days on market
$1,749,000
Price reduced by ↓ $150,00085 High Street, Winchester, MA 01890
$466/sqft · 9 days on market
$1,650,000
Price reduced by ↓ $100,0001 Overlook Way, Winchester, MA 01890
$458/sqft · 46 days on market
$2,999,000
5 Forest Cir, Winchester, MA 01890
$612/sqft · 16 days on market
$1,450,000
67-69 Hemingway St, Winchester, MA 01890
11 days on market
$1,549,000
50 Holland Street, Winchester, MA 01890
$587/sqft · 102 days on market
$2,400,000
Price reduced by ↓ $200,0007 Lakeview Terrace, Winchester, MA 01890
$679/sqft · 53 days on market
$1,049,900
28 Olive St, Winchester, MA 01890
$589/sqft · 12 days on market
$2,195,000
Price reduced by ↓ $104,000276 High Street, Winchester, MA 01890
$438/sqft · 216 days on market
$2,299,000
Price reduced by ↓ $100,00054 Squire Road, Winchester, MA 01890
$517/sqft · 89 days on market
$2,175,000
Price reduced by ↓ $75,0009 Plymouth Rd, Winchester, MA 01890
$534/sqft · 125 days on market
$3,299,000
1 Plymouth Rd., Winchester, MA 01890
$457/sqft · 38 days on market
$3,200,000
30 Willowdale Rd, Winchester, MA 01890
$557/sqft · 54 days on market
$1,985,000
30 Surrey Rd, Winchester, MA 01890
$468/sqft · 25 days on market
$2,650,000
18 Middlesex St, Winchester, MA 01890
$506/sqft · 17 days on market
$1,999,000
Price reduced by ↓ $50,00021 Amberwood Dr, Winchester, MA 01890
$492/sqft · 32 days on market
Houses for sale in Winchester, MA: market at a glance
As of November 7, 2026, there are 44 single-family homes for sale in Winchester, MA, with a median list price of $1,749,000. In August 2026, the median sale price for homes in Winchester, MA (all home types) was $1,480,000, up 0.3% from a year earlier.
- Houses for sale
- 44
- Median list price
- $1,749,000
- Median sale price (August 2026, all home types)
- $1,480,000
- Median days on market (August 2026, all home types)
- 47 days
Common questions about Winchester, MA real estate
How many single-family homes are for sale in Winchester, MA?
As of November 7, 2026, there are 44 single-family homes for sale in Winchester, MA.
What is the median single-family home price in Winchester, MA?
The median list price of single-family homes for sale in Winchester, MA is $1,749,000. Homes (all home types) that sold in August 2026 had a median sale price of $1,480,000, up 0.3% from a year earlier.
How long do homes take to sell in Winchester, MA?
Homes (all home types) in Winchester, MA that sold in August 2026 had a median of 47 days on market. Single-family homes currently for sale show a median of about 43 days on market.
Brokerage Information
eXp Realty
165 Thorndike Street, Lowell, MA, 01852
(978) 267-7409
License #9589109
Market Area Served
Boston, Fitchburg, Worcester, Waltham, Lowell, Norwood, Burlington, Framingham, Newton and many more.
The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.





























